CA2652506A1 - Derive antibiotique d'un glycopeptide - Google Patents

Info

Publication number

CA2652506A1

CA2652506A1 CA002652506A CA2652506A CA2652506A1 CA 2652506 A1 CA2652506 A1 CA 2652506A1 CA 002652506 A CA002652506 A CA 002652506A CA 2652506 A CA2652506 A CA 2652506A CA 2652506 A1 CA2652506 A1 CA 2652506A1

Authority

CA

Canada

Prior art keywords

hydrogen

optionally substituted

lower alkyl

compound

substituted

Prior art date

2006-05-26

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical class O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 title abstract description 30
• 150000001875 compounds Chemical class 0.000 claims abstract description 240
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 214
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 128
• 239000001257 hydrogen Substances 0.000 claims abstract description 126
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 69
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 61
• 150000003839 salts Chemical class 0.000 claims abstract description 52
• 239000012453 solvate Substances 0.000 claims abstract description 49
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 41
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 37
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 33
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 28
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 26
• 125000004450 alkenylene group Chemical group 0.000 claims abstract description 25
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
• 125000001424 substituent group Chemical group 0.000 claims description 54
• 125000003545 alkoxy group Chemical group 0.000 claims description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000005647 linker group Chemical group 0.000 abstract description 3
• 125000002837 carbocyclic group Chemical group 0.000 abstract 1
• 239000000126 substance Substances 0.000 description 269
• -1 N-hexyl Chemical group 0.000 description 241
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 58
• 239000000203 mixture Substances 0.000 description 57
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 43
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 36
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
• 238000009472 formulation Methods 0.000 description 25
• 239000004480 active ingredient Substances 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
• 108010059993 Vancomycin Proteins 0.000 description 23
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 23
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
• 125000003118 aryl group Chemical group 0.000 description 22
• 239000007787 solid Substances 0.000 description 20
• 229960003165 vancomycin Drugs 0.000 description 19
• MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 19
• 238000000034 method Methods 0.000 description 16
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 13
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 125000000753 cycloalkyl group Chemical group 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• 239000002244 precipitate Substances 0.000 description 12
• 239000003826 tablet Substances 0.000 description 12
• 125000001072 heteroaryl group Chemical group 0.000 description 11
• 239000011541 reaction mixture Substances 0.000 description 11
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• PNAFKSHCMVAYFW-UHFFFAOYSA-N 3,5-dichloro-n-(5-formylpyridin-3-yl)benzamide Chemical compound ClC1=CC(Cl)=CC(C(=O)NC=2C=C(C=O)C=NC=2)=C1 PNAFKSHCMVAYFW-UHFFFAOYSA-N 0.000 description 9
• XUJFOSLZQITUOI-UHFFFAOYSA-N 4-(trifluoromethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)F)C=C1 XUJFOSLZQITUOI-UHFFFAOYSA-N 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• 229920002472 Starch Polymers 0.000 description 9
• 239000008107 starch Substances 0.000 description 9
• 235000019698 starch Nutrition 0.000 description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• 238000004440 column chromatography Methods 0.000 description 8
• 239000013078 crystal Substances 0.000 description 8
• 238000001914 filtration Methods 0.000 description 8
• XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 8
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
• 125000003282 alkyl amino group Chemical group 0.000 description 7
• 125000003277 amino group Chemical group 0.000 description 7
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 7
• 235000019359 magnesium stearate Nutrition 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 239000002253 acid Substances 0.000 description 6
• 125000002252 acyl group Chemical group 0.000 description 6
• 230000000845 anti-microbial effect Effects 0.000 description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• 210000004899 c-terminal region Anatomy 0.000 description 6
• 239000002775 capsule Substances 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 208000015181 infectious disease Diseases 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• 230000004048 modification Effects 0.000 description 6
• 238000012986 modification Methods 0.000 description 6
• 229910052760 oxygen Inorganic materials 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
• 238000011282 treatment Methods 0.000 description 6
• DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical class NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
• 125000003710 aryl alkyl group Chemical group 0.000 description 5
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
• 239000001913 cellulose Substances 0.000 description 5
• 229920002678 cellulose Polymers 0.000 description 5
• 235000010980 cellulose Nutrition 0.000 description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
• 239000003910 polypeptide antibiotic agent Substances 0.000 description 5
• 150000003254 radicals Chemical class 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000006188 syrup Substances 0.000 description 5
• 235000020357 syrup Nutrition 0.000 description 5
• 241000194033 Enterococcus Species 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• 241000191967 Staphylococcus aureus Species 0.000 description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
• 229910052799 carbon Inorganic materials 0.000 description 4
• ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
• 125000004093 cyano group Chemical group *C#N 0.000 description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
• 239000004615 ingredient Substances 0.000 description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
• 239000011780 sodium chloride Substances 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• 125000004434 sulfur atom Chemical group 0.000 description 4
• 239000000454 talc Substances 0.000 description 4
• 229910052623 talc Inorganic materials 0.000 description 4
• 235000012222 talc Nutrition 0.000 description 4
• 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 4
• 125000005425 toluyl group Chemical group 0.000 description 4
• 229960001572 vancomycin hydrochloride Drugs 0.000 description 4
• LCTORFDMHNKUSG-XTTLPDOESA-N vancomycin monohydrochloride Chemical compound Cl.O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 LCTORFDMHNKUSG-XTTLPDOESA-N 0.000 description 4
• LDSQQXKSEFZAPE-UHFFFAOYSA-N 2-piperidin-4-ylethanol Chemical compound OCCC1CCNCC1 LDSQQXKSEFZAPE-UHFFFAOYSA-N 0.000 description 3
• QIFKBPZQJAFODS-UHFFFAOYSA-N 3-bromo-3-(1,3-dioxolan-2-yl)-4h-pyridine Chemical compound O1CCOC1C1(Br)CC=CN=C1 QIFKBPZQJAFODS-UHFFFAOYSA-N 0.000 description 3
• BNSMIGOOHPJIFH-UHFFFAOYSA-N 5-(1,3-dioxolan-2-yl)pyridin-3-amine Chemical compound NC1=CN=CC(C2OCCO2)=C1 BNSMIGOOHPJIFH-UHFFFAOYSA-N 0.000 description 3
• 239000004215 Carbon black (E152) Substances 0.000 description 3
• VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
• RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 229910006074 SO2NH2 Inorganic materials 0.000 description 3
• 229910006069 SO3H Inorganic materials 0.000 description 3
• 239000002262 Schiff base Substances 0.000 description 3
• 150000004753 Schiff bases Chemical class 0.000 description 3
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 241000191940 Staphylococcus Species 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 3
• 239000004599 antimicrobial Substances 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
• 125000005129 aryl carbonyl group Chemical group 0.000 description 3
• 125000004104 aryloxy group Chemical group 0.000 description 3
• 125000004429 atom Chemical group 0.000 description 3
• 239000002585 base Substances 0.000 description 3
• 239000011230 binding agent Substances 0.000 description 3
• 125000004432 carbon atom Chemical group C* 0.000 description 3
• 239000001768 carboxy methyl cellulose Substances 0.000 description 3
• 239000003153 chemical reaction reagent Substances 0.000 description 3
• 229940125782 compound 2 Drugs 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
• 201000010099 disease Diseases 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 150000002367 halogens Chemical class 0.000 description 3
• 229930195733 hydrocarbon Natural products 0.000 description 3
• 150000002430 hydrocarbons Chemical class 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 239000000314 lubricant Substances 0.000 description 3
• 229960003085 meticillin Drugs 0.000 description 3
• 239000013081 microcrystal Substances 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
• 238000007911 parenteral administration Methods 0.000 description 3
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
• 125000003107 substituted aryl group Chemical group 0.000 description 3
• 238000012360 testing method Methods 0.000 description 3
• GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
• ZEBIFXFBSFYXKP-JXMROGBWSA-N (e)-3-(4-chlorophenyl)-n-[1-(2,2-diethoxyethyl)-2-oxopyrimidin-4-yl]prop-2-enamide Chemical compound O=C1N(CC(OCC)OCC)C=CC(NC(=O)\C=C\C=2C=CC(Cl)=CC=2)=N1 ZEBIFXFBSFYXKP-JXMROGBWSA-N 0.000 description 2
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
• YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• ZXKKOFJYPRJFIE-UHFFFAOYSA-N 4-(trifluoromethoxy)benzoyl chloride Chemical compound FC(F)(F)OC1=CC=C(C(Cl)=O)C=C1 ZXKKOFJYPRJFIE-UHFFFAOYSA-N 0.000 description 2
• IFXJEJPFSHQXKA-UHFFFAOYSA-N 4-amino-1-(2,2-diethoxyethyl)pyrimidin-2-one Chemical compound CCOC(OCC)CN1C=CC(N)=NC1=O IFXJEJPFSHQXKA-UHFFFAOYSA-N 0.000 description 2
• NGUVGKAEOFPLDT-UHFFFAOYSA-N 5-bromopyridine-3-carbaldehyde Chemical compound BrC1=CN=CC(C=O)=C1 NGUVGKAEOFPLDT-UHFFFAOYSA-N 0.000 description 2
• 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
• 239000005711 Benzoic acid Substances 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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